Pentaciklusos indolalkaloid-hibridek szintézise

Translated title of the contribution: Synthesis of pentacyclic indolealkaloid hybrids

J. Kökösi, Zsuzsanna Likó, Árpád Kiss, Benjamin Podányi, I. Hermecz

Research output: Contribution to journalArticle

Abstract

Hybrid compounds were synthesized combining the structural features of two isomer natural indolealkaloids rutaecarpine (1) and nauklefine (3). These aza-bioisosteric analogues are the first representatives of a new heterocyclic ring system. Two alternative reaction routes were developed for the synthesis of pentacyclic compounds (4,5) in which the key step is the Fischer indolization of the 6-phenylhydrazono-dipyrido[1,2-a;4,3-d]pyrimidine-11-ones. In the case of E-ring substituted derivatives we performed the synthesis via preparation and chemical transformation of pyrido[1,2-a]pyrimidine-4-ones (14,15) to 2-substituted-3-aza-rutaecarpines (17-20). Finally, the nucleophilic displacement of the chlorine atom of 2-chloro-3-aza-rutaecarpine (18) by dialkylaminoetbylamine provided the 2-amino-substituted derivative (20) having improved physico-chemical properties and increased antitumour activity. The new compounds are characterized by UV, IR, 1H, 13C nmr spectroscopy.

Original languageHungarian
Pages (from-to)188-190
Number of pages3
JournalMagyar Kemiai Folyoirat, Kemiai Kozlemenyek
Volume107
Issue number5
Publication statusPublished - 2001

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Derivatives
Chlorine
Isomers
Chemical properties
Spectroscopy
Atoms
rutecarpine
pyrimidine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Pentaciklusos indolalkaloid-hibridek szintézise. / Kökösi, J.; Likó, Zsuzsanna; Kiss, Árpád; Podányi, Benjamin; Hermecz, I.

In: Magyar Kemiai Folyoirat, Kemiai Kozlemenyek, Vol. 107, No. 5, 2001, p. 188-190.

Research output: Contribution to journalArticle

Kökösi, J. ; Likó, Zsuzsanna ; Kiss, Árpád ; Podányi, Benjamin ; Hermecz, I. / Pentaciklusos indolalkaloid-hibridek szintézise. In: Magyar Kemiai Folyoirat, Kemiai Kozlemenyek. 2001 ; Vol. 107, No. 5. pp. 188-190.
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